Anthraquinone derivative.



Ur'rn PA nnr FIG.

PAUL THOMASOHElVSKI, OF ELBERFELD, GERMANY, ASSIGNOR TO FAR- 'BENFABRIKEN VORM. FRIEDR. BAYER &\ 00., OF ELBERFELD, GER- MANY, A CORPORATION OF GERMANY.

ANTHRAQUINONE DERIVATIVE.

Specification of Letters Patent.

Patented Ma 7, 1907.

Application filed February 11f1907. Serial No. 356,811.

SKI, doctor of philosophy, chemist, a citizen of the German Empire, residing at Elberfeld, Kingdom of Prussia, Germany, have invented new and useful Improvements in Anthraquinone Derivatives, of which the following is a specification.

I have found that acetylized secondary alkylaminoor arylaminoanthraquinones are converted into new compounds by treatment with alkalics; The new anthraquinone derivatives most probably contain a pyridone ring formed by intramolecular condensation. They are more or-less colored crystalline compounds of basic character practically insoluble in water and soluble in yridin and in concentrated sulfuric acid Wit from a yellow to red color. Y

The acetylized derivatives of second ary alkylaminoor arylaminoanthraquinones (the parent materials for the production of the new compounds) .can obtained by boiling the secondary alkylaminoorarylaminoanthraquinones with from twice to five times their weight of acetic anhydrid.

The invention is illustrated by the following examples, the parts being by weight:

Example I.1O parts of finely powdered acetyl alpha-mathylaminoanthraquinone are heated to boilingwith 500 parts of water and 10 parts of an aqueous solution of NaOH of After 6 hours, heating" the amorphous body is transformed into crystals. It

is filtered off and washed. The new compound crystallizes froni pyridinin the shape of yellow needles. The reaction takes place in accordance with the following equation, a pyridone ringbeing most probably closed:

Hots; N-CHa concentrated sulfuric acid with a dull-green Example II.5 parts of actyl-lf-methylamino-4-nitroanthraquinone are boiled for 3 hours with a solution of 2 parts of sodium in parts of anhydrous methyl alcohol. By the action of the sodium methylate the nitro group in 4 position is replaced by the methoxy group. The compound obtained has most probably the formula:

Example III.'1-methylamino-4-paratolylaminoanthraquinone is converted into the 'acetylized derivative by heating to boiling one part of it with one part of. acetic anhydrid for one hour. The mixture of. the reaction is thendiluted with 2 parts of alcohol and the precipitate thus obtained (garnetred crystals) is filtered off. It is soluble in color. One part of 1-acetylniethylamino-4- paratolylaminoanthraquinone is heated to boiling with a solution of one part of N aOH in 10. parts of alcohol for 3 hours. The new compound deposits While cooling in the sha e of dark-red crystals. It has most probably the following formula:

OH N-OH3 I (lg I i l I ll M CO I NHCtHl OH3 Analyst's.

Calculated for O fi O N Found.

C== 78.68% I 78.81% 5 H=-,4.92% i 5.24%

it crystallizes'from pyridin theshape of bronze-like leaflets. unmordanted and chromed woolbluish-red fast shades.

Its sulfonic acid dyes no .a test portion dissolveswithoutany residue in dilute caustic soda. The melt'is'then diluted with water and the dyestufl. sulfonic acid is filtered off; 'Itsalkaline'salts are solubl e in water with a crimson-redcolor.

The process is carried out in'ananalogous manner if other of the above mentioned anthraquinone derivatives, orother alkalies be used.

Condensation I i a i product (pg:- Solutlon in figiggaag g ggg g sulfurlc acid.

,Actybalplia- Yellow use; Yellow Yellow with methyl-amino- I v yellow flue-- 'anth'raqulnone. I w I I .rescence. i'maleet l-'1.5 ,-d i v 'e'needles. orange yel Yellowlshwith anthraquinone- "r resc ence.

dcetyl-alph'aicellow crystals. Yellow...'.;. Yellow with- ,para-tolylamie I out fluoresnoanthraquicence.

, -none. I 1-acetyline1:hyl-''Bronze likecrys Violet-red.. Violet-red, amino-4-paratal s. I I cofpper red tolylaminoana ter addithraquinone. I tlon of boric I I acid.

1 acetyhnethyl- Brownlsh -'yel Crlmson-red Yellow, yellow amino-.4-dilow prisms. v 4 fluorescence methylamlnoafter addianthraquinone Y tlon of bor'lc (ehlorhydrate); acid.

'as hereinbefore described.

I witnesses.

seam:

Having now described my invention and 4.0

in .what manner the same is to be performed.

what I claim as new and desire to secure by Letters Patent is 1. The herein described antl'n'acene compoundswhich can be obtained-by treating acetylized secondary alkylamino- .or' 'arylaminoanthraquinones with alkalies; which anthracene compounds are crystalline and practically insoluble in water; and soluble in pyridin and in concentrated sulfuric, acid with from a yellow to red 6010 2. The he'rei'n described anthraoene com pound which can be obtained by treatingv 1 acetylm'ethylamino e 4 paratolylaminoan thraquinone with alkalies, which anthraoene'..

r, substantially compound forms-bronze-like leaflets soluble in 'pyridin' with a violet-red color and in concentrated sulfuric acid with a violet-red color; andjwhich in the shape of its sulfonic acid dissolves in dilute alkall'with a crimson red color, and dyes unmordanted and In testimony whereof I have hereunto se my hand in the presence of two subscribing I bruit lHOMASGHEWS K I. [1,;- s,] Witnesses? v Or'ro Korma;

J. A. RITTERsnAUs.

chromed wool bluish-red shades, substantially as hereinbefore described. 1 

